Bronsted acid catalyzed asymmetric reduction of 2- and 2,9-substituted 1,10-phenanthrolines

被引：41

作者：

Metallinos, Costa ^{[1
]}

Barrett, Fred B. ^{[1
]}

Xu, Shufen ^{[1
]}

机构：

[1] Brock Univ, Dept Chem, St Catharines, ON L2S 3A1, Canada

来源：

SYNLETT | 2008年 / 05期

关键词：

reduction; phenanthroline; Bronsted acid; enantioselective; organocatalysis;

D O I：

10.1055/s-2008-1032103

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Several 2- and 2,9-substituted 1,10-phenanthrolines are reduced asymmetrically for the first time using a Hantzsch dihydropyridine in the presence of BINOL-derived phosphoric acid catalysts. The best results are obtained with phenanthrolines bearing unbranched or nitrogen-containing alkyl groups in the 2- or 2,9-positions, which afford chiral octahydrophenanthrolines in a range of yields (40-88%) and good to excellent levels of enantiomeric purity (78-99% ee).

引用

页码：720 / 724

页数：5

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